Benzyl Alcohol → HCID 86753769, compound

Participants

Reaction Steps

To a solution of (5R,6S,7S)-6-(4-fluorophenyl)-3-(5-cyano-2-isopropoxy-phenyl)-1-oxaspiro[4.4]non-3-ene-7-carboxylic acid (128 mg, 0.304 mmol) in toluene (2 mL) were added N,N,-diisopropylethylamine (64 μL, 0.367 mmol) followed by diphenylphosphoryl azide (73 μl, 0.339 mmol). The mixture was stirred for 30 minutes at room temperature and then for 1 hour at 100° C. Benzyl alcohol (63 μL, 0.609 mmol) was then added, and the mixture was stirred for 18 hours at 100° C. The cooled mixture was diluted with ethyl acetate (30 mL), washed with saturated sodium hydrogencarbonate solution, saturated brine solution, dried (Na2SO4), and evaporated. Silica gel chromatography eluting with 30% ethyl acetate/hexane afforded the title compound; yield 49 mg. The 400 MHz NMR spectrum in CD3OD was in accord with the desired structure.

Provenance & Evidence